IL28961A - 3,1-benzothiazine derivatives and process for their manufacture - Google Patents

3,1-benzothiazine derivatives and process for their manufacture

Info

Publication number: IL28961A
Authority: IL; Israel
Prior art keywords: general formula; compound; chloro; methyl; reacted
Prior art date: 1966-11-26

Application number

IL28961A

Other languages

English (en)

Original Assignee

Hoechst Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1966-11-26

Filing date

1967-11-17

Publication date

1971-11-29

1967-11-17 Application filed by Hoechst Ag filed Critical Hoechst Ag

1971-11-29 Publication of IL28961A publication Critical patent/IL28961A/en

Links

238000000034 method Methods 0.000 title claims description 11
230000008569 process Effects 0.000 title claims description 11
238000004519 manufacturing process Methods 0.000 title claims description 7
CURPPPMZYPWREO-UHFFFAOYSA-N 2h-3,1-benzothiazine Chemical class C1=CC=CC2=NCSC=C21 CURPPPMZYPWREO-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 50
239000002253 acid Substances 0.000 claims description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 13
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 13
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 8
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
235000013877 carbamide Nutrition 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000004423 acyloxy group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
150000005840 aryl radicals Chemical class 0.000 claims description 4
150000007514 bases Chemical class 0.000 claims description 4
150000002540 isothiocyanates Chemical class 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
230000009467 reduction Effects 0.000 claims description 3
150000003672 ureas Chemical class 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000005265 dialkylamine group Chemical group 0.000 claims description 2
229910052987 metal hydride Inorganic materials 0.000 claims description 2
150000004681 metal hydrides Chemical class 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims description 2
230000000506 psychotropic effect Effects 0.000 claims 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
229910052794 bromium Inorganic materials 0.000 claims 2
229910052736 halogen Inorganic materials 0.000 claims 2
150000002367 halogens Chemical class 0.000 claims 2
239000008194 pharmaceutical composition Substances 0.000 claims 2
125000004429 atom Chemical group 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
-1 amino, mercapto Chemical class 0.000 description 42
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 27
238000002844 melting Methods 0.000 description 27
230000008018 melting Effects 0.000 description 26
239000013078 crystal Substances 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 13
239000000243 solution Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 11
229960004217 benzyl alcohol Drugs 0.000 description 11
239000000047 product Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
150000001298 alcohols Chemical class 0.000 description 10
239000007858 starting material Substances 0.000 description 10
239000003208 petroleum Substances 0.000 description 9
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
150000003585 thioureas Chemical class 0.000 description 8
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
239000008164 mustard oil Substances 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
235000019445 benzyl alcohol Nutrition 0.000 description 5
230000003001 depressive effect Effects 0.000 description 5
150000007522 mineralic acids Chemical class 0.000 description 5
150000007524 organic acids Chemical class 0.000 description 5
239000008096 xylene Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000012024 dehydrating agents‎ Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000000605 extraction Methods 0.000 description 4
235000005985 organic acids Nutrition 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
208000010513 Stupor Diseases 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
150000003938 benzyl alcohols Chemical class 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
KUTKEONJUFGRFD-UHFFFAOYSA-N 6-chloro-N-ethyl-4-methyl-4-phenyl-1H-3,1-benzothiazin-2-imine Chemical compound C(C)NC1=NC2=C(C(S1)(C1=CC=CC=C1)C)C=C(C=C2)Cl KUTKEONJUFGRFD-UHFFFAOYSA-N 0.000 description 2
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
GMEGXJPUFRVCPX-UHFFFAOYSA-N butylthiourea Chemical compound CCCCNC(N)=S GMEGXJPUFRVCPX-UHFFFAOYSA-N 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
125000004985 dialkyl amino alkyl group Chemical group 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
POXAIQSXNOEQGM-UHFFFAOYSA-N propan-2-ylthiourea Chemical compound CC(C)NC(N)=S POXAIQSXNOEQGM-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
230000002048 spasmolytic effect Effects 0.000 description 2
230000004936 stimulating effect Effects 0.000 description 2
239000001117 sulphuric acid Substances 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
150000003568 thioethers Chemical class 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
KWZYIAJRFJVQDO-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl KWZYIAJRFJVQDO-UHFFFAOYSA-N 0.000 description 1
ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 1
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical compound CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
GOEXOFDHFDONEZ-UHFFFAOYSA-N 2-[chloro(diphenyl)methyl]aniline Chemical compound NC1=CC=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 GOEXOFDHFDONEZ-UHFFFAOYSA-N 0.000 description 1
WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
RGTMILHZLXZRGF-UHFFFAOYSA-N 2-methylpropylthiourea Chemical compound CC(C)CNC(N)=S RGTMILHZLXZRGF-UHFFFAOYSA-N 0.000 description 1
UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical class C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
UQHVLBXSTLXKNM-UHFFFAOYSA-N 4-phenyl-4H-3,1-benzothiazine Chemical compound C1(=CC=CC=C1)C1SC=NC2=C1C=CC=C2 UQHVLBXSTLXKNM-UHFFFAOYSA-N 0.000 description 1
MYWACSYZSHUARJ-UHFFFAOYSA-N 4H-thiopyrano[3,2-b]pyridine Chemical class N1=C2C(=CC=C1)SC=CC2 MYWACSYZSHUARJ-UHFFFAOYSA-N 0.000 description 1
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
IHACQZMICIAUIN-UHFFFAOYSA-N 6-chloro-4-methyl-4-phenyl-3,1-benzothiazin-2-amine Chemical compound NC1=NC2=C(C(S1)(C1=CC=CC=C1)C)C=C(C=C2)Cl IHACQZMICIAUIN-UHFFFAOYSA-N 0.000 description 1
PGSDPKVMKMOURZ-UHFFFAOYSA-N 6-chloro-4-methyl-4-phenyl-3,1-benzoxazin-2-amine Chemical compound O1C(N)=NC2=CC=C(Cl)C=C2C1(C)C1=CC=CC=C1 PGSDPKVMKMOURZ-UHFFFAOYSA-N 0.000 description 1
MDTPDVFYVSGPHJ-UHFFFAOYSA-N 6-chloro-N-ethyl-4,4-dimethyl-1H-3,1-benzoxazin-2-imine Chemical compound C(C)NC1=NC2=C(C(O1)(C)C)C=C(C=C2)Cl MDTPDVFYVSGPHJ-UHFFFAOYSA-N 0.000 description 1
KRZZKXYTSCQNNE-UHFFFAOYSA-N 6-chloro-n,4-dimethyl-4-phenyl-3,1-benzoxazin-2-amine Chemical compound O1C(NC)=NC2=CC=C(Cl)C=C2C1(C)C1=CC=CC=C1 KRZZKXYTSCQNNE-UHFFFAOYSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
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GDSRWTIEHLMYEU-UHFFFAOYSA-N C(C)N(CCC1=NC2=C(C(S1)(C1=CC=CC=C1)C)C(=C(C=C2)Cl)N)CC Chemical compound C(C)N(CCC1=NC2=C(C(S1)(C1=CC=CC=C1)C)C(=C(C=C2)Cl)N)CC GDSRWTIEHLMYEU-UHFFFAOYSA-N 0.000 description 1
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QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
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LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 1
BPEQQWOLRWZJJO-UHFFFAOYSA-N N-benzyl-6-chloro-4-methyl-4-phenyl-1H-3,1-benzoxazin-2-imine Chemical compound C(C1=CC=CC=C1)NC1=NC2=C(C(O1)(C1=CC=CC=C1)C)C=C(C=C2)Cl BPEQQWOLRWZJJO-UHFFFAOYSA-N 0.000 description 1
GMEHFXXZSWDEDB-UHFFFAOYSA-N N-ethylthiourea Chemical compound CCNC(N)=S GMEHFXXZSWDEDB-UHFFFAOYSA-N 0.000 description 1
206010029333 Neurosis Diseases 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical group OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
UHGKYJXJYJWDAM-UHFFFAOYSA-N Propylthiourea Chemical compound CCCNC(N)=S UHGKYJXJYJWDAM-UHFFFAOYSA-N 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical class S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 description 1
208000032140 Sleepiness Diseases 0.000 description 1
206010041349 Somnolence Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000005012 alkyl thioether group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 1
GSEZYWGNEACOIW-UHFFFAOYSA-N bis(2-aminophenyl)methanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1N GSEZYWGNEACOIW-UHFFFAOYSA-N 0.000 description 1
XFZGERCUSZURML-UHFFFAOYSA-N bis[2-(diethylamino)ethyl] carbonate Chemical compound CCN(CC)CCOC(=O)OCCN(CC)CC XFZGERCUSZURML-UHFFFAOYSA-N 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
208000037765 diseases and disorders Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229960001484 edetic acid Drugs 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
ANNNGOUEZBONHD-UHFFFAOYSA-N ethyl phenylmethanesulfonate Chemical compound CCOS(=O)(=O)CC1=CC=CC=C1 ANNNGOUEZBONHD-UHFFFAOYSA-N 0.000 description 1
IBYCYJFUEJQSMK-UHFFFAOYSA-N etifoxine Chemical compound O1C(NCC)=NC2=CC=C(Cl)C=C2C1(C)C1=CC=CC=C1 IBYCYJFUEJQSMK-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
150000003977 halocarboxylic acids Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
LMYQWQCDUHNQLF-UHFFFAOYSA-N hexylthiourea Chemical compound CCCCCCNC(N)=S LMYQWQCDUHNQLF-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
UGVPKMAWLOMPRS-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].CC[CH2-] UGVPKMAWLOMPRS-UHFFFAOYSA-M 0.000 description 1
OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
IGHVUURTQGBABT-UHFFFAOYSA-N methyl 2-amino-5-chlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1N IGHVUURTQGBABT-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000004899 motility Effects 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
LASJRIHCUCYPGY-UHFFFAOYSA-N n,n-diethyl-2-isothiocyanatoethanamine Chemical compound CCN(CC)CCN=C=S LASJRIHCUCYPGY-UHFFFAOYSA-N 0.000 description 1
YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000036632 reaction speed Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000012991 xanthate Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients

Landscapes

Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Air Bags (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL28961A 1966-11-26 1967-11-17 3,1-benzothiazine derivatives and process for their manufacture IL28961A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0050772		1966-11-26

Publications (1)

Publication Number	Publication Date
IL28961A true IL28961A (en)	1971-11-29

Family

ID=7104056

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL28961A IL28961A (en)	1966-11-26	1967-11-17	3,1-benzothiazine derivatives and process for their manufacture

Country Status (12)

Country	Link
US (1)	US3502666A (cs)
AT (4)	AT276413B (cs)
BE (1)	BE707100A (cs)
CH (2)	CH567008A5 (cs)
DE (1)	DE1670773A1 (cs)
FI (1)	FI49306C (cs)
FR (2)	FR1571289A (cs)
GB (1)	GB1214000A (cs)
IL (1)	IL28961A (cs)
NL (1)	NL6715789A (cs)
NO (1)	NO130685C (cs)
SE (1)	SE357563B (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5277132A (en) *	1975-12-23	1977-06-29	Fuji Photo Film Co Ltd	Preparation of thiazine derivative

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1545820A1 (de) *	1965-06-03	1969-12-11	Hoechst Ag	Verfahren zur Herstellung von 3,1-Benzothiazin-Derivaten

1966
- 1966-11-26 DE DE19661670773 patent/DE1670773A1/de active Pending
1967
- 1967-11-16 US US683454A patent/US3502666A/en not_active Expired - Lifetime
- 1967-11-17 IL IL28961A patent/IL28961A/en unknown
- 1967-11-21 NL NL6715789A patent/NL6715789A/xx unknown
- 1967-11-23 NO NO170666A patent/NO130685C/no unknown
- 1967-11-24 FI FI673170A patent/FI49306C/fi active
- 1967-11-24 CH CH344670A patent/CH567008A5/xx not_active IP Right Cessation
- 1967-11-24 AT AT1063267A patent/AT276413B/de active
- 1967-11-24 AT AT1103868A patent/AT276417B/de active
- 1967-11-24 CH CH1653267A patent/CH523275A/de not_active IP Right Cessation
- 1967-11-24 SE SE16147/67A patent/SE357563B/xx unknown
- 1967-11-24 AT AT1103668A patent/AT276415B/de active
- 1967-11-24 AT AT1103768A patent/AT276416B/de active
- 1967-11-27 BE BE707100D patent/BE707100A/xx unknown
- 1967-11-27 FR FR1571289D patent/FR1571289A/fr not_active Expired
- 1967-11-27 GB GB53960/67A patent/GB1214000A/en not_active Expired
1968
- 1968-02-23 FR FR141044A patent/FR7359M/fr not_active Expired

Also Published As

Publication number	Publication date
FI49306C (fi)	1975-05-12
FR7359M (cs)	1969-10-20
AT276416B (de)	1969-11-25
CH523275A (de)	1972-05-31
FI49306B (cs)	1975-01-31
CH567008A5 (cs)	1975-09-30
AT276415B (de)	1969-11-25
BE707100A (cs)	1968-05-27
AT276417B (de)	1969-11-25
NO130685C (cs)	1975-01-22
NL6715789A (cs)	1968-05-27
DE1670773A1 (de)	1970-12-23
NO130685B (cs)	1974-10-14
GB1214000A (en)	1970-11-25
FR1571289A (cs)	1969-06-20
SE357563B (cs)	1973-07-02
AT276413B (de)	1969-11-25
US3502666A (en)	1970-03-24

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NO150638B (no)	1984-08-13	Analogifremgangsmaate for fremstilling av terapeutisk aktive, basiske ethere
US5389630A (en)	1995-02-14	Diamine compound and brain protecting agent containing the same
US3725404A (en)	1973-04-03	2-amino-4,4-di-substituted-4h-3,1-benzoxazines
US3227713A (en)	1966-01-04	Azine derivatives
US2852510A (en)	1958-09-16	Heterocyclic compounds and process for producing same
NO159384B (no)	1988-09-12	Analogi-fremgangsmaate for fremstilling av terapeutisk aktive n6-(1-indanyl) adenosin-derivater.
US3931216A (en)	1976-01-06	Process for the manufacture of 2-arylamino-2-imidazoline derivatives and their salts
US3417085A (en)	1968-12-17	3,1-benzothiazines and 3,1-benzoxazines
NO791334L (no)	1979-10-23	Fremgangsmaate ved fremstilling av 1,3-diaryl-2-imino-imidazolidiner og -2-imino-hexahydro-pyrimidiner
US2643255A (en)	1953-06-23	Method of preparing piperazine compounds and a new type of compound produced thereby
US2794810A (en)	1957-06-04	Aminoalkyl cycloalkylcarbamates
GB2101580A (en)	1983-01-19	Allophanoylpiperazine compounds
US2659732A (en)	1953-11-17	Quaternary ammonium salts of dialkyl aminoalkyl xanthene-9-carboxylates and the production thereof
IL28961A (en)	1971-11-29	3,1-benzothiazine derivatives and process for their manufacture
IL43749A (en)	1977-06-30	Cyclopropylmethylamine derivatives of n-containing heterocyclic compounds their production and pharmaceutical compositions containing them
US4166852A (en)	1979-09-04	Piperazino-pyrimidines and their use as spasmolytic agents
US3527762A (en)	1970-09-08	Piperidine derivatives
US2857383A (en)	1958-10-21	Amino esters of thianaphthenealkanoic acids
US20030069417A1 (en)	2003-04-10	Novel synthesis and crystallization of piperazine ring-containing compounds
US4139632A (en)	1979-02-13	Psychotropic 2-trifluoromethyl-10-[3-(3-hydroxy-pyrrolidino)-propyl]-phenothiazine compounds
IL28432A (en)	1972-01-27	New fantasy histories of the tetracycline type and processes for their preparation
US3334115A (en)	1967-08-01	Basically substituted ureas and salts thereof
US3370066A (en)	1968-02-20	Substituted methylenedioxybenzamides
DK144270B (da)	1982-02-01	Analogifremgangsmaade til fremstilling af n-carbamoyl-2-phenylethensulfonamider
DE69713128T2 (de)	2003-03-20	4-(1-piperazinyl)benzosäurederivate, verfahren zu ihrer herstellung und ihre therapeutischen verwendungen